Taylor Montgomery was a sophomore at Foothill High School when he approached the tee on a 330-yard par-4 at Chimera GC outside Las Vegas. Competing in a qualifier for the following day’s match, Montgomery pulled driver out of his bag in an attempt to drive the green on the uphill hole.

The instinctively athletic teenager with a consistently splendid short game was working through struggles off the tee, and they reared their head on his first attempt. The drive sailed out-of-bounds, requiring him to now re-tee and hit his third shot.

This time, he selected the prudent play and pulled out his 3-wood.

It was the right choice. His balled rolled into the hole for the unlikeliest of birdies.

“He pipes this driver and he hits it out of bounds, way right,” recalled Paul DeSantis, who coached Montgomery in high school golf and basketball. “I’m like, ‘Come on, man, all you’ve got to do is hit 5-iron or whatever.’

“He just laughs the whole time. He re-tees and it doesn’t leave the flagstick. This is into a 15-mph wind … Three-wood from that distance back then is crazy. Can’t find it, checked the hole and there it was. Best birdie I’ve ever seen.”

Fast forward to the LECOM Suncoast Classic in February 2020. In the fifth start of his rookie Korn Ferry Tour season, Montgomery played his first 17 holes Sunday in 9 under to assume the lead. The 18th hole at Lakewood National GC is a long par-4 that provides a demanding finish. Even Montgomery, one of the Korn Ferry Tour’s longest hitters, had to hit 5-iron for his second shot.

Once again, the ball sailed right and out of bounds. It was the type of miscue in a crucial situation that can send a player asunder. How did Montgomery respond? Hitting his fourth shot from the same spot, he stuck it to 2 feet, staving off further disaster and making a bogey that secured a third-place finish, two shots behind winner Andrew Novak.

“That out-of-bounds is not really in play,” recalled Jon Sinclair, Montgomery’s swing coach for the past five years. “And then to turn right around and hit the same 5-iron within 2 feet of the hole … that pretty much sums up Taylor.”

He makes the most of second chances, a fact that was confirmed this year when he recovered from the heartbreak of missing out on his PGA TOUR card not once, but twice, last season. He finished 26th on the Korn Ferry Tour’s points list in both the Regular Season and Finals, falling one spot short of graduation each time.

Less than a year later, Montgomery’s promotion to the PGA TOUR is secure thanks to nine top-25s in 14 starts, including a pair of runners-up. Montgomery, 27, will receive that long-awaited TOUR card Sunday evening in Omaha, Nebraska, at the Pinnacle Bank Championship presented by Aetna, the Korn Ferry Tour Regular Season finale.

“He just decided, ‘Hey, I wasn’t ready, and now this year I’m ready,’” Sinclair said. “And he’s clearly ready.”

**

Montgomery arrived in Omaha last year ranked 24th on the Points List and one week away from his TOUR card.

A missed cut allowed two players to pass him, however.

He was in an even better position a month later, arriving at the Korn Ferry Tour Championship ranked 14th on the Finals points list. With six holes remaining in the second round, he was one stroke inside the cut line as he tried to repeat what happened in Omaha.

He played the next six holes in 12 over par. Two days later, Justin Lower got up-and-down for par on the 72nd hole to pass Montgomery and earn the final card. Lower took the final spot by making a 2-foot putt on the final hole.

Montgomery was watching from a golf shop in Las Vegas when Lower offered words of encouragement on the broadcast.

“Taylor Montgomery, if you’re listening, I’ve been in your spot before and I know it’s not any fun,” he said. “You’re a heck of a player, and just keep grinding. Good things will happen.”

Lower was right. History will not repeat itself in Omaha. The number crunchers and statisticians have ensured Montgomery. He earned enough points to cross the fail-safe threshold for TOUR status with a runner-up at last month’s Price Cutter Charity Championship presented by Dr Pepper. What a relief.

“I thought I had it locked up both times,” Montgomery said. “That was brutal. That was not a lot of fun. I didn’t think I could finish 26 twice; it’s pretty hard to do.”

Then a reflective pause.

“Now I’m in.”

**

If any pro were positioned to overcome this particularly cruel nature of a competitive sting, perhaps it was Montgomery. At different junctures throughout his junior and amateur days and early professional career, keeping the ball in play proved a challenge. There are memories of playing entire tournaments hitting no more than 2-iron off the tee.

“I didn’t hit my driver good enough to compete at any level,” Montgomery assessed.

It got so troublesome that he was pulled from the UNLV starting lineup after early college success.

“The first two years, he was the best on the team and won a couple times,” said Harry Hall, a college teammate and fellow Korn Ferry Tour pro. “The last couple years, he couldn’t make the team, couldn’t figure out his game. He’s always been a great chipper and putter, and he makes a lot of clutch putts … he’s worked really hard with Jon Sinclair, and together they’ve found a way to get it to the green, and from there he knows what he’s doing.”

Approximately five years ago, Montgomery began working with Sinclair, who concurred that driver was the immediate concern – “he truly couldn’t keep it between the white stakes when I first met him, to be honest.”

Sinclair described the issue as not in technique but in matchups – “There was confusion in what he was wanting to do with the club; that was the only issue.”

Throughout his junior and amateur days, Montgomery liked to swing hard; DeSantis remembers 137 mph swing speed as a high school freshman.

Montgomery knew that to reach an elite level, though, he needed to dial it back. Shortly before meeting Sinclair, he worked through a swing adjustment where he flattened his wrist angle at the top of his backswing. It meant a 10-12 mph reduction in clubhead speed, but as Sinclair noted, “We’re not out there trying to be the long drive champion.”

“He could put more force in the club back then if he would extend that wrist versus flatten it out like he does now so much,” Sinclair said, “but how much speed does he need?”

He averaged 302 yards off the tee last season (No. 85 on Tour), and 311.6 yards this season (No. 43).

Both seasons, he has ranked 11th or better in both putting and scrambling, aligning with DeSantis’ description of a high school-aged Montgomery.

“He didn’t care where he hit it because he knew he could chip and putt and beat everybody to death,” DeSantis said. “His short game was the best in the country; he won the state championship hitting the ball out of sage bushes. The philosophy with Taylor was, ‘Go ahead, let him hit it as hard as he can. It doesn’t matter where he hits it; he’s going to find a way to get the ball in the hole.’

“Now he’s understood the value of hitting fairways. The other day, we went out to the high school, he’s 124-125 mph on the Trackman, We give him crap about it; he’s like, ‘Aw, I’m getting old.’ What he’s saying is, ‘I’ve learned to dial it back so I can hit it in the fairway.’”

The coach’s trust was rooted in a belief that Montgomery would outwork his competitors. DeSantis remembers lengthy nighttime chipping and putting sessions that required light from his car; some went so long that the battery would drain. He tells stories of Montgomery hitting 3-woods for two hours in 30 mph winds before heading to a basketball game that night.

Montgomery describes his greatest basketball strength as “fouling.” DeSantis remembers him as a gritty competitor with a motor who would guard the opponent’s best player and willingly rebound.

This ethos translates to golf.

“If he goes out there and hates the fact that he made a 6 on a par 4 and starts working for it, now you know you have something special,” said DeSantis of a philosophy in evaluating junior golfers.

“That’s always been Taylor. He’s got to fail and figure it out; he’s just got to go through it. He’ll figure it out because he wants it.”

Montgomery grew up around high rollers. His dad Monte is general manager at Shadow Creek GC, a Vegas club notoriously known for its memorable gambling games. He shadowed money games from a young age; he remembers a time when poker player Phil Ivey challenged a rival to a $1 million bet on a single hole.

“I think he had to give the guy a shot, but he ended up winning anyway,” Montgomery said. “I was out there the next day, he walks up to me, ‘Hey kid, take my new car for a ride.’ He had bought a brand-new Mercedes McLaren for $500,000.”

There was also the time when a young Montgomery, age 7 or 8, ran into a certain shoe marketer.

“My dad brought me into the clubhouse and said, ‘You’re gonna meet Michael Jordan,’ and I was so excited,” Montgomery said. “Probably the biggest sports name ever. So I walk in and he goes, ‘Hey, what’s up, kid?’ and I go, ‘Hey, Michael,’ and he goes, ‘What the heck are you wearing?’

“I had AND1 shoes because I played basketball. They were 40 bucks; I wasn’t going to pay $200 for a pair of shoes. I told him I couldn’t afford his shoes. He said, ‘Your shoes are too expensive.’ He said, ‘You’ve got a point.’”

The rift wouldn’t ruin the relationship. Jordan was following on PGATOUR.COM as Montgomery shot 63 on the final day of 2019 Q-School to secure guaranteed Korn Ferry Tour starts. The basketball legend texted Monte in excitement.

If Montgomery’s character is any indication, his fan base will continue to grow as he takes the stage as a TOUR member.

For all his Korn Ferry Tour success, a victory has eluded him, some near-misses more painful than others. Hall was in the gallery for the final moments of this year’s AdventHealth Championship, as Montgomery led Trevor Cone by one stroke on the 72nd hole.

Montgomery made bogey while Cone made birdie to win.

“I was distraught, and he handled it great,” Hall said. “I remember watching him in his interview and he said, ‘It’s just golf, and the kids are the most important,’ and he signed the autographs.

“That shows his character underneath.”

Perhaps indicative of the perspective that allowed Montgomery to overcome the wrong side of the bubble – twice – to earn the Korn Ferry Tour’s ultimate victory, a PGA TOUR card.

“There are some shots I hit where I think, ‘You need to reassess your life,’ and others like, ‘Wow, I can’t be beat,’” Montgomery said. “It’s a crazy game, it spins you in circles, and I don’t think that will ever change.”